Journal of Natural Products 最新文献_第3页

Macrocyclic Compounds with Diverse Skeletons from the Roots of Myrica nana and Their Spasmolytic Activity. 杨梅根中不同骨架的大环化合物及其解痉活性。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-26 DOI: 10.1021/acs.jnatprod.4c01209

Liyuan Zhang, Ziliang Wang, Yuxiao Li, Shenghai Yang, Wenting Chen, Yanhong Li, Kai Tian, Yan Yuan, Xishan Bai, Xiangzhong Huang

引用次数: 0

Cardenolides in Asclepias syriaca Seeds: Exploring the Legacy of Tadeus Reichstein. 叙利亚阿斯克莱皮亚种子中的松香内酯：探索Tadeus Reichstein的遗产。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-18 DOI: 10.1021/acs.jnatprod.4c00960

Paola Rubiano-Buitrago, Ronald A White, Amy P Hastings, Frank C Schroeder, Anurag A Agrawal, Christophe Duplais

{"title":"Cardenolides in Asclepias syriaca Seeds: Exploring the Legacy of Tadeus Reichstein.","authors":"Paola Rubiano-Buitrago, Ronald A White, Amy P Hastings, Frank C Schroeder, Anurag A Agrawal, Christophe Duplais","doi":"10.1021/acs.jnatprod.4c00960","DOIUrl":"10.1021/acs.jnatprod.4c00960","url":null,"abstract":"The common milkweed Asclepias syriaca is widespread in North America and produces cardenolide toxins that deter herbivores by targeting the transmembrane enzyme Na+/K+-ATPase. In 1979, Nobel Laureate Tadeus Reichstein elucidated the structure of novel cardenolides isolated from A. syriaca roots and proposed structures for several other cardenolides that could not be confirmed. In this study, we investigate the cardenolide composition of A. syriaca seeds, focusing on their abundance and in vitro inhibitory potency on the sensitive porcine Na+/K+-ATPase and that of the highly resistant large milkweed bug, Oncopeltus fasciatus. We identify five previously unreported cardenolides (1-5), three of which are predominantly found in seeds, in addition to the known syrioside (6), aspecioside (7), and the 2-thiazoline ring-containing cardenolide labriformin (8). Glucopyranosyl-allomethylosyl-12-deoxy aspecioside (5) is distinguished by lack of oxidation at C-12, and compounds 2, 3, 6, and 8 contain a rare 1,4-dioxane motif. Inhibitory efficacy of the isolated cardenolides for sensitive and resistant enzymes appears to be correlated. Finally, we confirmed the structure of compound 2, originally proposed by Tadeus Reichstein, and are pleased to share his original 1979 handwritten manuscript.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"49-57"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142845311","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Cyclopenta[bc]benzopyran Derivatives and Limonoids from Aglaia edulis with Cytotoxic and Anti-DENV Activity. 环戊烷[bc]苯并吡喃衍生物及柠檬酮类化合物的细胞毒性及抗denv活性研究

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2025-01-05 DOI: 10.1021/acs.jnatprod.4c01194

Ping Yi, Jian-Fei Qiu, Xiao-Meng Yang, Fei-Fei Chen, Jue Yang, Juan Liu, Jun Jin, Lian-Xin Qi, Xiao-Jiang Hao, Jia-Hong Wu, Chun-Mao Yuan

引用次数: 0

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2025-01-09 DOI: 10.1021/acs.jnatprod.4c01109

Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang, Haji A Aisa

引用次数: 0

Uncovering Hericenones from the Fruiting Bodies of Hericium erinaceus through Interdisciplinary Collaboration. 通过跨学科合作从猴头菌子实体中发现猴头菌烯。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-26 DOI: 10.1021/acs.jnatprod.4c01018

Junhong Wang, Jing Wu, Ryo Yamaguchi, Kaoru Nagai, Chengwei Liu, Jae-Hoon Choi, Hirofumi Hirai, Xiaonan Xie, Shoji Kobayashi, Hirokazu Kawagishi

{"title":"Uncovering Hericenones from the Fruiting Bodies of Hericium erinaceus through Interdisciplinary Collaboration.","authors":"Junhong Wang, Jing Wu, Ryo Yamaguchi, Kaoru Nagai, Chengwei Liu, Jae-Hoon Choi, Hirofumi Hirai, Xiaonan Xie, Shoji Kobayashi, Hirokazu Kawagishi","doi":"10.1021/acs.jnatprod.4c01018","DOIUrl":"10.1021/acs.jnatprod.4c01018","url":null,"abstract":"Hericium erinaceus is an edible and medicinal mushroom. Previously, we found hericenones C-H from the fruiting bodies and erinacines A-I from the mycelia of the fungus. These compounds stimulated nerve growth factor (NGF) synthesis both in vitro and in vivo; some have been suggested to be effective in the prevention and treatment of dementia. Recently, the total synthesis of hericenones C-H and their derivatives (1-4) was reported by one of the authors. We considered that the chemical synthetic route would also be reasonable as a biosynthetic pathway of the compounds. Based on the hypothesis, we investigated the endogenous existence of synthetic intermediates and products of the chemical synthesis in the fruiting bodies. The n-hexane-soluble part of the fruiting bodies of H. erinaceus was fractionated, and all the fractions were subjected to a product ion scan and multiple reaction monitoring (MRM) analysis by LC-MS/MS and compared to the authentic synthesized compounds. The analysis indicated the endogenous existence of 1-4 and the dehydrated form of 2 or 3. The dehydrated form was elucidated to be (Z)-5 by chemical synthesis, and a plausible biosynthetic pathway was proposed.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"80-85"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773572/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142890686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Iodide Enhances the Production of Pseurotin D over Pseurotin A by Inverting the Preference for the S_N2 versus the S_N2' Product in the Final Nonenzymatic Step. 碘化物通过逆转SN2和SN2'产物在最后非酶步骤中的偏好，促进假素D比假素A的产生

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-23 DOI: 10.1021/acs.jnatprod.4c01128

Yukyung Choi, Yeongseo Kim, Jin Wook Cha, Gyu Sung Lee, Huong T Pham, Men Thi Ngo, Saegun Kim, Chung Sub Kim, Kyo Bin Kang

引用次数: 0

An Unexpected Activity of a Minor Cannabinoid: Cannabicyclol (CBL) Is a Potent Positive Allosteric Modulator of Serotonin 5-HT_1A Receptor. 一种意想不到的小大麻素活性：大麻环醇（CBL）是5-羟色胺5-HT1A受体的一种有效的阳性变构调节剂。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2025-01-15 DOI: 10.1021/acs.jnatprod.4c00977

Mehdi Haghdoost, Yvonne DePorre, Max Figi, Scott Young, Caitlyn Krebs, Marcel O Bonn-Miller

{"title":"An Unexpected Activity of a Minor Cannabinoid: Cannabicyclol (CBL) Is a Potent Positive Allosteric Modulator of Serotonin 5-HT1A Receptor.","authors":"Mehdi Haghdoost, Yvonne DePorre, Max Figi, Scott Young, Caitlyn Krebs, Marcel O Bonn-Miller","doi":"10.1021/acs.jnatprod.4c00977","DOIUrl":"10.1021/acs.jnatprod.4c00977","url":null,"abstract":"Cannabicyclol ((±)-CBL), a minor phytocannabinoid, is largely unexplored, with its biological activity previously undocumented. We studied its conversion from cannabichromene (CBC) using various acidic catalysts. Montmorillonite (K30) in chloroform at room temperature had the highest yield (60%) with minimal byproducts. Key reaction conditions, such as solvent, temperature, and time, significantly impacted the yield. The structure of (±)-CBL was confirmed via X-ray crystallography. Stability studies showed that (±)-CBL and its MCT oil dilution remain stable at 25-40 °C for three months. Radioligand binding assays revealed high affinity of CBL for the 5-HT1A receptor but weak interaction with CB1 and CB2 receptors. At 10 μM and 1 μM, (±)-CBL inhibited [3H]-8-hydroxy-DPAT binding to 5-HT1A by 75% and 20%, respectively. Functional assays showed that (±)-CBL acts as a weak agonist at high concentrations but a potent positive allosteric modulator of serotonin-induced activation at low concentrations. At 4 μM, (±)-CBL increased serotonin-induced β-arrestin recruitment from 20% to 80%. This unique modulatory profile highlights the potential of (±)-CBL in drug discovery targeting serotonin receptors.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"58-66"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11774245/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142981966","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Derivatization of Microcystins Can Increase Target Inhibition while Reducing Cellular Uptake. 微囊藻毒素的衍生物化可以增加对目标的抑制作用，同时减少细胞的吸收。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-10-20 DOI: 10.1021/acs.jnatprod.4c00688

Laura L Sallandt, Clemens A Wolf, Sabine Schuster, Heike Enke, Dan Enke, Gerhard Wolber, Timo H J Niedermeyer

{"title":"Derivatization of Microcystins Can Increase Target Inhibition while Reducing Cellular Uptake.","authors":"Laura L Sallandt, Clemens A Wolf, Sabine Schuster, Heike Enke, Dan Enke, Gerhard Wolber, Timo H J Niedermeyer","doi":"10.1021/acs.jnatprod.4c00688","DOIUrl":"10.1021/acs.jnatprod.4c00688","url":null,"abstract":"Microcystins, a large family of nonribosomal cyclic heptapeptides known for their hepatotoxicity, are among the best-studied cyanobacterial toxins. Recently, they have been discussed as leads for the development of anticancer drug substances. Their main mode-of-action is inhibition of the eukaryotic serine/threonine protein phosphatases 1 and 2A. Unlike many cytotoxins that can cross cell membranes by passive diffusion, microcystins depend on active uptake via organic anion transporting polypeptides 1B1 or 1B3. Both phosphatase inhibition and transportability strongly depend on the structure of the individual microcystin. Here, we present how chemical modification of positions 2 and 4 of the microcystin core structure can alter these two properties. Aiming to reduce transportability and increase phosphatase inhibition, we used pharmacophore modeling to investigate the phosphatase inhibition potential of microcystins derivatized with small molecules containing a variety of functional groups. The respective derivatives were synthesized using click chemistry. We discovered that some derivatized microcystins can address a yet undescribed subpocket of the protein phosphatase 1. The derivatized microcystins were tested for phosphatase 1 inhibition and cytotoxicity on transporter-expressing cell lines, revealing that target inhibition and transportability of microcystins can independently be influenced by the physicochemical properties, especially of the residue located in position 2 of the microcystin. Derivatization with small acids or amino acids resulted in microcystins with a favorable ratio of inhibition to transportability, making these derivatives potentially suitable for drug development.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"3-14"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11773564/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142453368","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Chemical Basis of the Traditional Ayurvedic Detoxification Process of the Toxic Medicinal Plant Plumbago zeylanica. 传统阿育吠陀解毒过程的化学基础。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2025-01-03 DOI: 10.1021/acs.jnatprod.3c00975

Ankur Kumar Tanwar, Debanjan Chatterjee, Neha Jain, Shivam Sharma, Kulbhushan Tikoo, Inder Pal Singh

{"title":"Chemical Basis of the Traditional Ayurvedic Detoxification Process of the Toxic Medicinal Plant Plumbago zeylanica.","authors":"Ankur Kumar Tanwar, Debanjan Chatterjee, Neha Jain, Shivam Sharma, Kulbhushan Tikoo, Inder Pal Singh","doi":"10.1021/acs.jnatprod.3c00975","DOIUrl":"10.1021/acs.jnatprod.3c00975","url":null,"abstract":"Certain medicinal plants utilized in the traditional ayurvedic system are poisonous when used raw, but are used following a detoxification process. The Ayurvedic Formulary of India (AFI) provides details about these detoxification (known as \"sodhana\") processes as per traditional procedures. This research endeavor aimed to uncover the fundamental principles underlying the detoxification approach applied to Plumbago zeylanica, commonly referred to as \"swet chitrak\", in which plumbagin is the primary toxic constituent. Both unprocessed and processed (detoxified) extracts as well as the detoxification media were subjected to analysis for secondary metabolites using different analytical techniques. This investigation revealed a reduction in plumbagin content, its conversion to epoxyplumbagin and zeylanone and a noteworthy decrease in cis- and trans-isoshinanolone during detoxification. Furthermore, it was confirmed that pure plumbagin when subjected to the same detoxification conditions, is partially converted into epoxyplumbagin, and that cis and trans-isoshinanolone showed interconversion. The current work establishes the chemical basis of the age-old traditional ayurvedic process of detoxification of P. zeylanica.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"15-23"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142925811","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Isolation and Characterization of Insecticidal Cyclotides from Viola communis. 从 Viola communis 中分离和鉴定杀虫环苷。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-05-15 DOI: 10.1021/acs.jnatprod.4c00168

Negin Khatibi, Yen-Hua Huang, Conan K Wang, Thomas Durek, Edward K Gilding, David J Craik

{"title":"Isolation and Characterization of Insecticidal Cyclotides from Viola communis.","authors":"Negin Khatibi, Yen-Hua Huang, Conan K Wang, Thomas Durek, Edward K Gilding, David J Craik","doi":"10.1021/acs.jnatprod.4c00168","DOIUrl":"10.1021/acs.jnatprod.4c00168","url":null,"abstract":"Cyclotides are cysteine-rich plant-derived peptides composed of 28-37 amino acids with a head-to-tail cyclic backbone and a knotted arrangement of three conserved disulfide bonds. Their beneficial biophysical properties make them promising molecules for pharmaceutical and agricultural applications. The Violaceae plant family is the major cyclotide-producing family, and to date, every examined plant from this family has been found to contain cyclotides. The presence of cyclotides in Viola communis was inferred by mass spectroscopy previously, but their sequences and properties had yet to be explored. In this study, the occurrence of cyclotides in this plant was investigated using proteomics and transcriptomics. Twenty cyclotides were identified at the peptide level, including two new members from the bracelet (Vcom1) and Möbius (Vcom2) subfamilies. Structural analysis of these newly identified peptides demonstrated a similar fold compared with cyclotides from the same respective subfamilies. Biological assays of Vcom1 and Vcom2 revealed them to be cytotoxic to Sf9 insect cell lines, with Vcom1 demonstrating higher potency than Vcom2. The results suggest that they could be further explored as insecticidal agents and confirm earlier general findings that bracelet cyclotides have more potent insecticidal activity than their Möbius relatives. Seven new cyclotide-like sequences were observed in the transcriptome of V. communis, highlighting the Violaceae as a rich source for new cyclotides with potential insecticidal activity. An analysis of sequences flanking the cyclotide domain in the various precursors from V. communis and other Violaceae plants revealed new insights into cyclotide processing and suggested the possibility of two alternative classes of N-terminal processing enzymes for cyclotide biosynthesis.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"24-35"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140920306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0